Merge pull request ckan#9186 from TomeCirun/fix/smtp-host-port-parsing

Fix SMTP TLS handshake failure when port is embedded in hostname

Author: amercader

changes/9186.bugfix

@@ -0,0 +1 @@
+Fix SMTP TLS error with embedded port

ckan/lib/mailer.py

@@ -7,6 +7,7 @@
 import socket
 import logging
 import mimetypes
+from urllib.parse import urlparse
 from time import time
 from typing import Any, Iterable, Optional, Tuple, Union, IO
 
@@ -97,8 +98,12 @@ def _mail_recipient(
     smtp_user = config.get('smtp.user')
     smtp_password = config.get('smtp.password')
 
+    host, port = _parse_smtp_server(smtp_server)
+    if not host:
+        raise MailerException('SMTP server hostname is not configured')
+
     try:
-        smtp_connection = smtplib.SMTP(smtp_server)
+        smtp_connection = smtplib.SMTP(host, port)
     except (socket.error, smtplib.SMTPConnectError) as e:
         log.exception(e)
         raise MailerException('SMTP server could not be connected to: "%s" %s'
@@ -310,3 +315,23 @@ def verify_reset_link(user: model.User, key: Optional[str]) -> bool:
     if not user.reset_key or len(user.reset_key) < 5:
         return False
     return key.strip() == user.reset_key
+
+
+def _parse_smtp_server(smtp_server: str) -> tuple[str | None, int]:
+    """Parse SMTP server that may include port.
+
+    Examples:
+        'smtp.example.com' -> ('smtp.example.com', 0)
+        'smtp.example.com:587' -> ('smtp.example.com', 587)
+        '[::1]:587' -> ('::1', 587)
+    """
+    default_port = 0
+
+    if "://" not in smtp_server:
+        smtp_server = f"smtp://{smtp_server}"
+
+    parsed = urlparse(smtp_server)
+    host = parsed.hostname
+    port = parsed.port or default_port
+
+    return host, port

ckan/tests/lib/test_mailer.py

@@ -413,3 +413,48 @@ def test_mail_user_with_attachments_no_media_type_provided(self, mail_server):
             "goals.png", "image/png",
         ]:
             assert item in msg[3]
+
+    @pytest.mark.ckan_config("smtp.server", ":")
+    def test_invalid_smtp_server_colon_only(self):
+        test_email = {
+            "recipient_name": "Bob",
+            "recipient_email": "b@example.com",
+            "subject": "Meeting",
+            "body": "Test",
+            "headers": {},
+        }
+
+        with pytest.raises(mailer.MailerException) as exc:
+            mailer.mail_recipient(**test_email)
+
+        assert "SMTP server hostname is not configured" in str(exc.value)
+
+    @pytest.mark.ckan_config("smtp.server", "localhost:1025")
+    def test_smtp_server_with_port(self, mail_server):
+        test_email = {
+            "recipient_name": "Bob",
+            "recipient_email": "b@example.com",
+            "subject": "Meeting",
+            "body": "Test",
+            "headers": {},
+        }
+
+        mailer.mail_recipient(**test_email)
+
+        msgs = mail_server.get_smtp_messages()
+        assert len(msgs) == 1
+
+    @pytest.mark.ckan_config("smtp.server", "[::1]:1025")
+    def test_smtp_server_ipv6_with_port(self, mail_server):
+        test_email = {
+            "recipient_name": "Bob",
+            "recipient_email": "b@example.com",
+            "subject": "Meeting",
+            "body": "Test",
+            "headers": {},
+        }
+
+        mailer.mail_recipient(**test_email)
+
+        msgs = mail_server.get_smtp_messages()
+        assert len(msgs) == 1